Acetic Acid → HCID 22220594, compound

Participants

Reaction Steps

Acetic acid (10 ml), saturated with anhydrous hydrogen bromide (gas) was added to [11,11-difluoro-1,7-bis(2-nitro-benzenesulfonyl)-1,4,7-triaza-cyclotetradec-4-yl]-phosphonic acid diethyl ester (311 mg, 0.41 mmol) contained in round-bottomed flask closed by glass stopper. The resulting mixture was allowed to stir for 18 hours at room temperature and then diethyl ether (50 ml) was added. The white precipitate which formed was allowed to settle to the bottom of the flask and the diethyl ether solution was decanted off. This white solid was re-dissolved in methanol, stirred with K2CO3 (solid) for 30 mins and the mixture was diluted with 100-ml ethyl acetate. The solids were removed by filtration and the filtrates were evaporated to give the title compound (239 mg, 94%) as white form. 1H NMR (CDCl3) δ 1.82–1.91 (m, 4H), 1.99–2.15 (m, 4H), 2.91 (t, 4H, J=5.1 Hz), 3.30–3.38 (m, 8H), 7.60–7.63 (m, 2H), 7.69–7.75 (m, 4H), 7.90–7.94 (m, 2H); 13C NMR (CDCl3) δ 23.25, 32.22, 32.57, 32.90, 50.22, 50.86, 50.96, 123.50, 124.60, 126.71, 129.89, 130.73, 132.02, 132.22, 134.27, 148.94; 19F NMR (CDCl3) δ −14.12 (t); ES-MS m/z 606.3 (M+H).

Provenance & Evidence